2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

• ChemBase ID: 170971
• Molecular Formular: C15H14N4O2
• Molecular Mass: 282.29726
• Monoisotopic Mass: 282.11167571
• SMILES: [nH]1c(=O)c2c(n(c3c1c(c(cn3)O)C)C1CC1)nccc2
• Canonical SMILES: Oc1cnc2c(c1C)[nH]c(=O)c1c(n2C2CC2)nccc1
• InChI: InChI=1S/C15H14N4O2/c1-8-11(20)7-17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9,20H,4-5H2,1H3,(H,18,21)
• InChIKey: DANIONWINZEYME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• IUPAC Traditional name: 2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• Synonyms: 11-Cyclopropyl-5,11-dihydro-3-hydroxy-4-methy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one; 3-Hydroxy Nevirapine

Database IDs

• CAS Number: 174532-82-2
• PubChem SID: 164226881
• PubChem CID: 10978907

CALCULATED PROPERTIES

• Acid pKa: 9.552424
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.046808
• LogD (pH = 7.4): 2.1686795
• Log P: 2.1844776
• Molar Refractivity: 79.4629 cm^3
• Polarizability: 28.741589 Å^3
• Polar Surface Area: 78.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 152-154°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H948630

A metabolite of Nevirapine (N391275).

REFERENCES

• Rettie, A., et al.: J. Biol. Chem., 263, 13733 (1988)
• Lamson, M., et al.: Biopharm. Drug Dispos., 20, 285 (1988)
• Guengerich, F., et al.: Chem. Res. Toxicol., 14, 611 (1988)
• Lu, W., et al.: Drug Metab. Dispos., 36, 1624 (1988)